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This qualitative study investigated the practices of two high school principals who built a culture in their schools focused on college and career readiness for all students, but in particular students from historically underserved backgrounds. The findings revealed that the principals engaged in a number of behaviors beginning with a personal, justice-oriented mindset that strove for equitable outcomes for all students through their leadership and advocacy. The career pathway structure supported teachers and faculty as they reinforced careers in their classrooms, through internships or mentorships, and exposing students to experiences and opportunities that contextualized their learning experiences. Both principals were mindful and deliberate in the programmatic structure as to not isolate or pre-determine paths for students.